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When the warm weather arrives, you want to be ready. That's why Westport Big & Tall offers dozens of different styles of big and tall men's shorts in a multitude of colors. For our taller customers, shorts are always a bit of a tricky proposition, so we make sure to carry the most trusted brands, including: Polo Ralph Lauren, Tommy Bahama, Cutter & Buck, Bills Khakis and more.
Please spend a few moments looking through our selection of big and tall men's shorts, making sure to note the array of colors for each style. For cool and casual, it's all right here.

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Cutter & Buck Flat-Front Stretch Tech Shorts
Tommy Bahama 4-Way Stretch Performance Shorts
Polo Ralph Lauren Flat-Front Seersucker Shorts
$89.50 $34.99
Tommy Bahama Flat-Front Plaid Shorts
Tommy Bahama Flat-Front Stretch Twill Shorts
Tommy Bahama Brushed Poplin Cargo Shorts
Polo Ralph Lauren Flat-Front Madras Linen Shorts
Cutter & Buck Flat-Front Twill Shorts
Tommy Bahama Print Stretch Boardshorts
Tommy Bahama Del Chino Shorts
$118.00 $49.99
Tommy Bahama Plaid Linen Shorts
$118.00 $51.99
Cutter & Buck Avalon Stripe Pleated Shorts
$95.00 $29.99
Tommy Bahama Solid Linen Shorts
$90.00 $26.99
Polo Ralph Lauren Corporal Cargo Shorts
$89.50 $39.99
Polo Ralph Lauren Gellar Vintage Chino Fatigue Shorts
$89.50 $43.99
Polo Ralph Lauren Pleated Chino Shorts
$85.00 $39.99
Tommy Bahama Print Cargo Boardshorts
Polo Ralph Lauren Flat-Front Chino Twill Shorts
$85.00 $44.99
Polo Ralph Lauren Flat Front Lightweight Chino Short
$98.00 $38.99
Callaway Flat-Front Heathered Twill Tech Shorts
$85.00 $33.99
Callaway Flat Front Microfiber Tech Shorts
$75.00 $39.99
Peter Millar Salem High Drape Performance Shorts
$118.00 $49.99
Peter Millar Flat Front Twill Winston Shorts
$118.00 $46.99
Bills Khakis Pleated Island Twill Shorts
$118.00 $59.99
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Big and Tall Mens Shorts: The Long and Short of It

Big and Tall Mens Shorts: The Long and Short of It

When it's time to sport those shorts, you want to make sure you are looking good. Just because it's not a suit, however, doesn't mean there aren't things to consider when picking our big and tall mens shorts that look just right. Let's take look at some of the main things to consider.

  • Pleats or Flat Front: While what's in style seems to go back and forth every year, you really can't go wrong with either the flat front or the pleats. If you choose pleats, however, you must be sure you get the right size waist. If the waist is too tight, it will pull on the pleats, fanning them out and making them look unflattering.
  • Solids or Patterns: When in doubt, you can't go wrong with solid colors. In fact, tans and beiges are pretty universal and appropriate in nearly every shorts-wearing situation. Colors and patterns are a little more tricky and usually reserved for more casual situation where a little fun and spontaneity are in order.
  • Elastic or Traditional Waist: Again, this is another situation where you have to make sure you get the waist size exactly right, particularly with elastic waistband shorts. Some guys prefer the comfort and give the elastic offers, but if you get them a little too small, it can actually accentuate your "love handles" and undermine the satisfaction you get from the comfort.
  • Cargos or Bermudas: While many people just see the pockets on cargo shorts as a a design element—and there is nothing wrong with that—don't forget they actually serve a functional purpose. For those who like to spend a good amount of time on the tennis court, they are ideal for holding extra tennis balls. If you are on the golf course, they are handy for extra tees and your scorecard. In most situations, either cargos or Bermudas and other non-pocket big and tall mens shorts will work just fine. Just remember how you like to spend your time before you buy.

Paired with jeans, khakis and even cargo shorts, polo shirts are among the most flexible ways to achieve that casual look without going too informal, which makes them perfect for nearly every occasion. Take advantage of the thorough selection of big and tall polo shirts at Westport Big & Tall.

As part of our continued commitment to customer service, we encourage you to contact us with any questions or concerns you have about any of our products, including our selection of polo shirts.

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